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COMMUNICATIONS TO THE EDITOR
Vol. 56
Reactions (9), ( l l ) , (13) and (15).-There does not seem to be any experimental evidence available for these reactions and in these cases also we have assigned values which are in agreement with the free radical mechanism.
none imide and aniline was catalyzed by ammonium chloride and did not go to completion; apparently an equilibrium was attained. Fluorenone anil was readily prepared by heating fluorenone imide and aniline.
DEPARTME~T OF CHEMISTRY THEJOHNS HOPKINS UNIVERSITY RECEIVED NOVEMBER 29, 1933 MD BALTIMORE,
Experimental Procedure Ammonolyis of Fluorenone.-Ten grams of fluorenonel was treated with 15 cc. of sodium-dried ammonia and allowed to stand at room temperature for several weeks. After the removal of ammonia the fluorenone imide was recrystallized from ligroin; m. p. 124", yield practically quantitative. Fluorenone M . - A mixture of 0.2 g. of fluorenonimide and 0.2 cc. of aniline was heated a t 120" for ninety minutes; ammonia was evolved. The yellow sirupy reaction product solidified on cooling and was recrystallized from petroleum ether; m. p. 87°.5 Ammonolysis of Fluorenone M . - A solution of 0.5 g. of fluorenone anil and 0.25 g. of ammonium chloride in dry liquid ammonia was heated a t 60' for four days. The ammonia was removed and the reaction product dissolved in boiling ligroin. On concentration of the solution 0.22 g. of fluorenone imide separated. From the mother liquor was isolated 0.15 g. of unchanged anil. No fluorenone imide was isolated in an experiment in which a solution of fluorenone anil in dry ammonia was heated a t 60" for twenty hours.
Ammonolysis of Fluorenone and Fluorenone A d BY LOUISA. PINCK AND GUIDOE HILBERT
Strain' has shown that ketones, such as acetophenone, on heating with ammonia a t 180" with aluminum chloride as a dehydrating agent, yield the corresponding ketimines. It has now been found that fluorenone imide can be prepared in excellent yield by the interaction of fluorenone and ammonia a t room temperature. This method is superior to that of Klieg12and is recommended for preparative purposes. Benzophenone, 9,9dichlorofluorene and 1,2-dichlorodibiphenyleneethane under similar conditions, however, do not react. Additional information on the behavior of Schiff bases in liquid ammonia3 was obtained in a study of the ammonolysis of fluorenone anil. This reaction leading to the formation of fluore(1) Strain, TxIs JOURNAL, 68, 820 (1930). (2) Kliegl, Ber., 43, 2488 (1910). see also Goldschmidt and Beuschel, A n n , 447, 203 (1926). (3) Strain, THISJOURNAL, 60, 2218 (1928).
(4) This was prepared according to the method of Schmidt and Wagner, Ber., 43, 1796 (1910). (3 kilos of technical fluorene yielded 2450 g. of pure fluorenone), which is practically identical with that recently published by Huntress, Hershberg and Cliff, THIS JOURNAL, S3, 2720 (1931). (5) Reddelien, Ber., 43, 2479 (1910); Schlenk and Bergmann,, A n n . . 463, 292 (1928).
RECEIVEDDECEMBER 8,1933 CONTRIBUTION FROM THE BUREAUOF CHEMISTRY AND SOILS u. DEPARTMENT OF AGRICULTURE WASHINGTON, D. C.
s.
COMMUNICATIONS T O T H E EDITOR KzO. The characteristics of the three types of adsorption on the promoted iron catalyst are as follows. Sir: Physical Adsorption. The adsorption of hydroBy making adsorption measurements in con- gen at 760 mm. pressure by a 10-cc. (about 22-g.) junction with our study of the catalytic conver- sample of catalyst that had been reduced by sion of ortlio to para hydrogen we have obtained hydrogen a t 450" addegassed a t the same temdata that seem to establish definitely the existence perature, was 5.0, 2.8 and 0.25 cc. at -196, of two types [see Benton, Trans. Faraday Soc., -1183 and - 1 4 4 O , respectively. The heat of 28,202 (1932), and Langmuir, Chem Rev., 13,188 adsorption calculated from isotherms was about (1933)l of activated and one type of physical 2000 calories. Type A Activated Adsorption.-Between -78 adsorption of hydrogen on the surface of an iron catalyst promoted with 1.3% ALO, and 1.59% and 0" apparent equilibrium could be obtained in
TWO TYPES OF ACTIVATED ADSORPTION OF HYDROGEN ON THE SURFACE O F A PROMOTED IRON SYNTHETIC AMMONIA CATALYST
